Annual Events
Due to COVID-19 most events are canceled for Summer 2020. Please check with event organizers to verify the event is happening.
All year long, Middlebury is home to great events planned by local businesses and organizations, many of which are free or low-cost. Outdoor movies under the stars, a festive parade down Main Street, a food truck festival with great live music…these are all events you can experience for yourself right here in Middlebury every year. Check them out!
Summer
Foodaroo
Food truck festival featuring live entertainment
Festival on the Green
A week-long free concert series on the town green
Sheldon Museum Pops Concert
Fireworks and concert to celebrate the 4th of July
St Stephen’s Peasant Market
The area’s largest flea market and rummage sale
Lion’s Club Auction
Auction and BBQ on the green
Downtown Block Party
A festive party on the closed off streets of Downtown Middlebury
Middlebury New Filmmakers Festival
A four-day event celebrating new filmmakers

Fall
Spooktacular
Trick-or-Treating down Main Street
Turkey Trot
Scenic 5k and 10k before Thanksgiving
Winter
WinterFest
Middlebury’s celebration of all things winter
Very Merry Middlebury
A month-long celebration of the holidays
Midd Night Stroll
Extended evening shopping, tasting and strolling
Spring
Middlebury Maple Run
A half marathon and fun run with the sweetest views
Memorial Day Parade
Marching bands, floats and more down Main Street